Fashion Plates: What to Wear For 29 Nights Out In Chicago

We know the drill—it's 6 p.m. on a Saturday night, and you have nothing to wear…and no idea where you're going. Thankfully, we've got you. We're sharing our inside scoop on Chicago's best places for late-night revelry. But, because we love you, we felt compelled to take it one step further. That's right, we're giving you 29 spots that guarantee a fabulous evening, plus all the outfits you'll need to show up looking like one of the (cooler) regulars.
Very soon, you'll be overlooking the Wrigley Building from a plush chair in Trump's sexy lounge Rebar, chatting about the notes in a Sonoma Valley Pinot, taste-testing craft beers with a tattoo-sleeved hipster, sucking down refreshingly sweet margaritas with girlfriends, and sipping bourbon with a scruffy, Liev Schreiber-look-alike. The best part? There are more than enough spots on this list to ensure your Friday, Saturday, and (let's get real), Thursday nights are fully booked for the next few months!
Sexy Hotel Lounges
With a name like Trump, it's pretty much guaranteed that the ambiance will be luxe, the drinks will be strong, and the real estate will be prime. Located on the mezzanine level of Trump International Hotel & Tower, Rebar is the perfect place to up the ante in a hot dress and stilettos — we're talking contemporary décor and wall-to-ceiling windows (with some seriously covetable views of the city), plus plenty of fine Italian suits at the bar. Grab a few girlfriends and order the Magic Winter Punchbowl, a take on traditional German glühwein.
Rebar, 401 North Wabash Avenue (between Kinzie Street and Wacker Drive); 312-644-0900.
And you thought rooftops were just for summer! Well, think again, because atop Raffaello Hotel, Drumbar’s sexy interior of tufted leather couches and warm dark wood paneling, is the perfect place to get cozy over an inspired cocktail menu. For colder nights, enjoy Tea Time with a few girlfriends — we suggest the Black & Red, a warm libation of red wine, Hennessy Black, cinnamon sticks, lemon sour, cardamom, nutmeg and orange served in a glass teapot.
Drumbar, 201 East Delaware Place (between Mies Van Der Rohe Way and Dewitt Place); 312-924-2531.
ROOF on theWit
We remember when ROOF on theWit hotel opened a few years ago in the Loop — the line of stilettos and miniskirts was down Lake Street — and we admit to wondering if its popularity would subside. But, that was before we went inside the 7,000-square-foot 27th floor lounge that literally oozes sex appeal. Lounge seating indoors is complemented by a retractable glass enclosure covering the outdoor patio, where bar stools line a long table and fireplace centerpiece. Snag a few of these seats with your girlfriends and be certain, the cocktails will come shortly thereafter.
ROOF, 201 North State Street (at Lake Street); 312-239-9501.
J. Parker
It’s probably too chilly to enjoy the stunning views of downtown and Lincoln Park from this perch above HotelLincoln, so duck inside and warm up with a classic cocktail: Mixologist Erin Hayes’ fall menu includes a variety of Kentucky Bourbon Trail-inspired libations like a Manhattan and Old Fashioned. Move on to the menu of small plates, overseen by chef Paul Virant from Perennial Virant on the first floor of the hotel. We like the sweet potato beignets and seared scallops with lemon butter and arugula.
J. Parker, 1816 North Clark Street (at Lincoln Avenue); 312-254-4747.
On the 26th floor of the Dana Hotel & Spa, Vertigo Sky Lounge is one of those spots you hit up to kick off a night that starts exactly as it begins: With plenty of dancing. The indoor/outdoor rooftop hosts live DJs nightly — plus, grab your faux fur coat and brave the elements for Vertigo’s annual December fire and ice winter patio returns.
Vertigo Sky Lounge, 2 West Erie Street (Between Dearborn and State streets); 312-202-6060.
Donna Karan Crepe-Jersey Dress, $1,995, available at Net-A-Porter; Vince Camuto Onyx French Clutch, $168, available at Vince Camuto; Alexis Bittar Swarovski Crystal Accented Orbiting Drop Earrings, $195, available at Saks Fifth Avenue; American Apparel Basic Leather Belt, $15, available at American Apparel; French75 Suede Stilettos, $125, available at Whistles.
Photo: Courtesy of Rebar Absolut_IntegratedTip-1
Off The Vine
RM Champagne Lounge
Sip Champagne and sparkling wines at this sexy lounge behind Nellcôte (the entrance is just off the alley on Green Street — follow the twinkling lights hanging along the brick wall). We dig the French-inspired menu of small items like a cheese plate or seafood platter for two. And, the candlelit ambiance is almost as cozy as this dreamy outfit.
RM Champagne Salon, 116 North Green Street (between Randolph Street and Washington Boulevard); 312-243-1199.
Boarding House
With master sommelier Alpana Singh steering the direction of Boarding House, we’re certain the opening this December will be worth the wait. Expect hundreds of offerings on the wine list and casual bar menu items, but what we’re most looking forward to is the late-night wine cellar down below.
Boarding House, 720 North Wells Street (between Superior and Huron streets); No Phone.
Bin 36
This wine-focused restaurant is all about fine dining food in a more casual atmosphere, coupled with plenty of wine tastings. With executive chef William Hewitt and wine director Brian Duncan at the helm, Bin 36 offers food and wine pairings that are enjoyable and accessible, and perfect for the gal who articulates her flavor preferences without the snooty accent. We like starting from a selection of wine flights like Sexy Reds and Think Pink. Fall in love with a particular glass? Take it home — they’re all available for purchase by the bottle in the market.
Bin 36, 339 North Dearborn Street (between Kinzie Street and Wacker Drive); 312-755-9463.
City Winery
Grab your girlfriends and sidle up to one of the many bars inside City Winery’s larger-than-life space (more than 30,000-square-feet!) to taste the range of wines made in-house. The space offers a 300-seat concert and performance venue, but we’re partial to the bar and dining scene, where you can order Mediterranean-inspired dishes to complement the vino. Plus, the knowledgeable staff can answer any questions about the varietals as they pour.
City Winery, 1200 West Randolph Street (between Racine Avenue and Ada Street); 312-733-9463.
This intimate wine bar is the perfect place to get cozy with girlfriends over a seasonal selection of wines from around the world and Spanish small plates, including artisanal cheeses you can’t resist. Located in the West Loop, the simply decorated space with dark wood floors and exposed brick wall might not be the best place for people watching, but when it comes to private conversations, these walls won’t talk.
Vera, 1023 West Lake Street (between Carpenter and Morgan Streets); 312-243-9770.
AllSaints Molotov Kenta Jeans, $120, available at AllSaints; Maison Martin Margiela High Heel Booties, $925, available at Shopbop; rag & bone Knit Long Sleeve Ribbed Tee, $105, available at Intermix; AE Faux Fur Vest, 469.95, available at AE; Coach Legacy Leather Medium Candace Carryall, $398, available at Coach.
Photo: Courtesy of RM Champagne
Non-Dive Dive Bars
Old Town Pour House
Old Town Pour House has all the offerings of a tavern: A nice long bar framed by multiple mounted flat screen TVs, high top tables, and comfort food dishes like mustard pretzel bites and baked truffle mac & cheese. But, it steps it up a notch with a list of 90 beers on tap that has the refined palates of ale, stout, and cider enthusiasts packing the joint nightly. A few brew-phobics in the crew? Order from the eight wines on tap or specialty cocktails. And, skip the full face of makeup for the soft sheen of Benefit’s new lip and cheek color, perfect to match Dana Rebecca’s delicate ring on your pinkie.
Old Town Pour House, 1419 North Wells Street (between Schiller Street and North Avenue); 312-477-2800.
The Kerryman
Judging by the number of Notre Dame T-shirts stuffed into booths at our last visit, we were ready to save The Kerryman for when our team is playing the Fighting Irish. But, as it turns out, the menu is more bistro burger than sports bar wings, and the fact that Skinnygirl Cocktails are on the Bloody Mary & Champagne Cocktail menu... well, it keeps us coming back.
The Kerryman, 661 North Clark Street (at Erie Street); 312-335-8121.
Three Aces
Don’t be fooled by the number of sleeve tattoos in this dark bar — it’s not just for hipsters or those who feel most at home riding a Harley. Yes, Little Italy’s “neighborhood joint” has quickly become a city-wide favorite. With chef Matt Troost cooking seasonal dishes (including the best cheeseburger in town, period), an extensive craft beer menu, and the Stones playing in the background, leave your stilettos at home for something a little more comfortable.
Three Aces, 1321 West Taylor Street (between Ada and Loomis streets); 312-243-1577.
Stout Barrel House & Gallery
Ever since Stout opened in River North this past summer, Manor — the glossy nightclub formerly occupying the space — is all but a distant memory. The new modern pub serves tasty American fare with a twist on a late-night menu until 3 a.m., and plenty of cocktails, to boot.
Stout Barrel House & Gallery, 642 North Clark Street (between Erie and Ontario streets); 312-475-1390.
Ada Street
From the guys who brought us DMK Burger Bar and Fish Bar, Michael Kornick and David Morton’s intimate lounge Ada Street may be a little off the beaten path (and you might just miss the tiny entrance if you’re not looking), but after entering the dark, candlelit corridor, expect to be pleasantly surprised by the sophisticated cocktails and savory dishes like crispy black-eyed peas. You might just be in for more than what’s on the menu at this sweet, romantic spot.
Ada St., 1664 North Ada Street (between Wabansia Avenue and Concord Place); 773-697-7069.
Aldo Orawin Ankle Boot, $150, available at Aldo; Topshop Snake Collarless Biker Jacket, $110, available at Topshop; Vince Drape Neck Blouse, $265, available at Intermix; Anya Hindmarch Valorie Glitter Clutch, $550, available at Scoop NYC; Citizens of Humanity Avedon Skinny Jean, $198, available at Zoe.
Photo: Courtesy of Old Town Pour House
Drink Your Dinner In Margs
Who doesn’t need a night to drink their weight in margaritas every once in a while? And, Mercadito is the perfect place to start sipping. Since you can plan to wait for the lust-worthy tacos and ceviches (even if you have a reservation), start with a traditional El Jimador Blanco margarita, or, our favorite, the Little Market — Olmeca Reosado tequila, fresh pineapple, chile guajillo, cilantro, and pico piquin (a spicy seasoning). The only thing hotter might just be this Marc Jacobs bag. Oh, when if the evening runs late, duck into Double A, a hush-hush hidden lounge below the restaurant.
Mercadito, 108 West Kinzie Street (between Clark Street and LaSalle Drive); 312-329-9555.
Big Star
Get there early, plan to stay late. Big Star fills up fast. So fast that even in the winter, when you’ve waited for about three rounds of margs, you’re so happy to score a table, who cares if it’s technically on the patio (which is now masquerading as part of the restaurant with giant heat lamps). The $3 whiskey shots are great, but nothing beats the tequila-based cocktails like a La Paloma or Classic Margarita. If, the next day, you’re left wondering whether it was the drinks that made you think those tacos were utterly delicious, trust us, they really are that good.
Big Star, 1531 North Damen Avenue (just south of North Avenue); 773-235-4039.
Cantina Laredo
Some might turn their noses up at a chain like Cantina Laredo, but the Casa Rita margarita with fresh lime juice doesn’t deserve to be snubbed. Bypass the hostess and head upstairs to the second bar/lounge. It’s quieter, so snag some window seats overlooking River North and order small plates in a cozy atmosphere.
Cantina Laredo, 508 North State Street (between Grand Avenue and Illinois Street); 312-955-0014.
Las Palmas
Wrap up a shopping trip in the chic Bucktown boutique district with drinks and traditional dishes like empanadas and pollo en mole. This time, skip the classic margs and opt for one of their house-made inspirations like the Pepinada, a fresh cucumber-lime margarita, or the Jarochita, a vanilla bean-pineapple infused tequila with fresh pineapple juice and Malibu rum.
Las Palmas Restaurant, 1835 West North Avenue (between Honore Street and Wolcott Avenue); 773-289-4991.
Adobo Grill
You can’t go wrong with Adobo’s legendary tableside guacamole, and the shaken Adobo Margaritas with fresh lime juice are nothing short of heavenly — plus, they’re sure to make you feel like it's your 21st birthday all over again (Not that you went to Cancun or anything!). The rustic décor will put you right at ease, and ready for a rousing evening of girl talk. Or more.
Adobo Grill, 1610 North Wells Street (Between North Avenue and Eugenie Street); 312-266-7999.
Stuart Weitzman Tipbootie, $495, available at Piperlime; Club Monaco Hilda Sweater Dress, $179.50, available at Club Monaco; Marc by Marc Jacobs Too Hot to Handle Small Top Handle, $428, available at Marc Jacobs; J.Crew Wide-Rib Wool Tights, $26.50, available at J.Crew; Benefit Cosmetics They’re Real! Mascara, $23, available at Benefit Cosmetics.
Photo: Courtesy of Mercadito
Celeb Spotting
Studio Paris
Countless celebs and big-name athletes have partied at Studio Paris while in town, and most enjoy a dinner downstairs at Paris Club before heading to the rooftop lounge for bottle service. The retractable glass roof is gorgeous during warmer months, but rain or shine, we love the booths with seats that lift up to store your clutch for safe keeping while you dance. How smart is that?
Studio Paris, 59 West Hubbard Street (between Dearborn and Clark streets), 312-595-0800.
Kelly Clarkson, The Fray, and The Black Keys have all been spotted walking through the 18-foot-high wrought iron gates of Nellcôte. The name comes from Villa Nellcôte, the mansion in Southern France where the Rolling Stones recorded Exile on Main Street in 1971, and the interior blends rock ‘n’ roll with glam accents like chandeliers and candlelight. Dinner is exceptional (house-milled flour boosts the pizzas to another level of tasty) and during the late night hours, a few celebs (we’re looking at you, Taylor Momsen) have been known to hop into the DJ booth and spin for guests.
Nellcôte, 833 West Randolph Street (between Green and Peoria streets); 312-432-0500.
The Underground
There’s not a celebrity we can think of who owner Billy Dec doesn’t know — Oprah, Obama, and we’re pretty sure we saw him in the background of a rerun of The Hills last weekend. Expect sightings galore at this underground lair (and staple Chicago nightlife venue).
The Underground, 56 West Illinois Street (Between Dearborn and Clark streets); 312-943-7600.
With names like Bill and Giuliana Rancic (he won The Apprentice, she’s interviewed countless celebs at red carpet events) and the Melman family (a.k.a., restaurant royalty), the place is bound to have a mix of good food and gussied-up celebrities. We love the Roman-style artichokes, which look like little boutonnières on the plate, and the understated but perfect flavors in Mama DePandi’s (Giuliana’s mom) Bucatini Pomodoro.
RPM Italian, 52 West Illinois Street (between Dearborn and Clark Streets); 312-222- 1888.
Kenneth Cole Urban Mesh Wide Cuff, $77.99, available at Piperlime; Elizabeth and James Chiffon Layer Blazer, $465, available at Intermix; BCBG Harlow Snake-Embossed Envelope Clutch, $78, available at BCBG; Sass & Bide The Dedication Embellished Cotton-Jersey Top, $290, available at Net-A-Porter; Joseph Leather Stretch Leggings, $680.63, available at My Wardrobe; KORS Michael Kors Aberly Metallic Genuine Snake Pump, $275, available at Michael Kors.
Photo: Courtesy of Studio Paris
Whiskey Bars
Always cursing that Saturday-night line outside the of-the-moment bar? Well, you’ll be thankful for it this time, otherwise you’re liable to walk right past Untitled's large, unmarked doors. Down below lies an establishment reminiscent of speakeasy and supper club joints. With more than 300 American and non-domestic whiskeys to choose from and live music on the main stage, you might just find a partner to swing dance with — good thing this skirt is perfect for a twirl.
Untitled, 111 West Kinzie Street (between Clark Street and LaSalle Drive), 312-880- 1511.
Longman & Eagle
With nearly 150 whiskeys to choose from, Longman & Eagle believes this is one libation not meant to sit on the shelf. On any given day, choose from 38 available $3 shots. Got a little too enthusiastic? Head upstairs and stay in one of the six comfortable, vintage-vibe guest rooms.
Longman & Eagle, 2657 North Kedzie Avenue (at Schubert Avenue); 773-276-7110.
The Southern
Along the busy stretch of Bucktown’s North Avenue, settle in and relax at this laidback bar boasting small batch bourbons and whiskeys, as well as traditional dishes like fried green tomatoes, Johnny cakes, and braised pork shank.
The Southern, 1840 West North Avenue (between Honore Street and Wolcott Avenue); 773-342-1840.
The Barrelhouse Flat
Whether it's scotch or bourbon, shaken or stirred, the whiskey cocktails coupled with a menu of creative dishes like spicy caramel wings and poutine, are enough to attract those all-American guys that Bruce Weber likes so much. Not looking to roll with the boys? Try the housemade punch or a seasonal cocktail in the two-story vintage-feeling bar.
The Barrelhouse Flat, 2624 North Lincoln Avenue (Between Wrightwood and Kenmore Avenues); 773-857-0421.
Sable Kitchen & Bar
The 1940s vibe in this modern space is evident in the Prohibition Era-style cocktails, served in vintage-looking glassware. Sable touts itself as serving one of the city’s “most complete libraries of amber spirits,” and they’re not lying — from single malt scotch whiskey and Irish whiskey to Japanese and Indian whiskeys, the selection is as long as last weekend's register line at Barneys. Check out Whiskey Wednesdays, where a pour is three-quarters of an ounce and the discussion highlights a certain distillery or philosophy.
Sable, 505 North State Street (Between Illinois and Grand Streets); 312-755-9704.
Vince Chunky-Knit Wool-Blend Sweater, $114, available at The Outnet; Amen Pleated Leather Skirt, $293, available at Far Fetch; Essie Good As Gold Nail Polish, $8, available at Macy’s; Rebecca Minkoff Patterned Woven M.A.C. Bag, $395, available at R29 Shops; Sam Edelman Women's Kit Ankle Boot, $115, available at Amazon.
Photo: Courtesy of Untitled

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